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Cheap flights from Wisconsin to Caribbean Islands from $72

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Wisconsin to Caribbean Islands departing on 1/15. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Wisconsin to Caribbean Islands

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
9:18 am - 7:43 pm
ORD
-
SJU
8h 25m1 stop
Multiple Airlines Logo
5:25 pm - 11:15 pm
SJU
-
ORD
7h 50m1 stop
$195Multiple Airlines
Sat, Feb 21 - Mon, Mar 2
JetBlue Logo
7:45 am - 6:05 pm
ORD
-
SJU
8h 20m1 stop
JetBlue Logo
11:06 am - 7:36 pm
SJU
-
ORD
10h 30m1 stop
$196JetBlue
Tue, Jan 13 - Fri, Jan 23
Spirit Airlines Logo
12:17 pm - 6:49 pm
ORD
-
SJU
4h 32mnonstop
Spirit Airlines Logo
1:22 pm - 4:37 pm
SJU
-
ORD
5h 15mnonstop
$197Spirit Airlines
Sat, Jan 24 - Wed, Feb 4
Frontier Logo
9:25 am - 4:21 pm
ORD
-
SJU
28h 56m1 stop
Frontier Logo
5:25 pm - 3:52 pm
SJU
-
ORD
24h 27m1 stop
$198Frontier
Sat, Feb 7 - Tue, Feb 10
Frontier Logo
1:54 pm - 2:25 am
ORD
-
SJU
10h 31m1 stop
Frontier Logo
2:54 am - 9:11 am
SJU
-
ORD
8h 17m1 stop
$201Frontier
Thu, Feb 19 - Sun, Feb 22
Spirit Airlines Logo
5:15 am - 1:38 pm
ORD
-
GCM
7h 23m1 stop
Spirit Airlines Logo
2:34 pm - 11:46 pm
GCM
-
ORD
10h 12m1 stop
$240Spirit Airlines
Sat, Jan 10 - Sat, Jan 17
Arajet Logo
5:45 am - 12:30 pm
ORD
-
PUJ
4h 45mnonstop
Arajet Logo
6:00 pm - 9:10 pm
PUJ
-
ORD
5h 10mnonstop
$249Arajet
Wed, Feb 25 - Sun, Mar 1
Arajet Logo
10:27 am - 5:12 pm
ORD
-
PUJ
4h 45mnonstop
Arajet Logo
5:47 am - 8:57 am
PUJ
-
ORD
5h 10mnonstop
$251Arajet
Sat, Feb 21 - Sat, Feb 28
Air Canada Logo
12:50 pm - 12:15 pm
ORD
-
NAS
22h 25m1 stop
Air Canada Logo
11:15 am - 11:43 am
NAS
-
ORD
25h 28m1 stop
$356Air Canada
Sat, Mar 28 - Fri, Apr 3
Air Canada Logo
6:04 pm - 12:15 pm
ORD
-
NAS
17h 11m2 stops
Air Canada Logo
1:25 pm - 8:00 am
NAS
-
ORD
19h 35m2 stops
$359Air Canada
Sat, Mar 28 - Fri, Apr 3

Sun Country Air flights from Wisconsin to Caribbean Islands

Our best Sun Country Air deals on Wisconsin to Caribbean Islands flight tickets
Sun Country Air
May 23
MSP7:35 amMinneapolis St Paul
5h 07m
SJU1:42 pmSan Juan Luis Munoz Marin Intl
May 30
SJU4:10 pmSan Juan Luis Munoz Marin Intl
6h 00m
MSP9:10 pmMinneapolis St Paul
$296
Find similar
Sun Country Air
May 23
MSP7:35 amMinneapolis St Paul
5h 07m
SJU1:42 pmSan Juan Luis Munoz Marin Intl
May 30
SJU4:10 pmSan Juan Luis Munoz Marin Intl
6h 00m
MSP9:10 pmMinneapolis St Paul
$297
Find similar
Sun Country Air
Dec 21
MSP1:17 pmMinneapolis St Paul
8h 03m
1 stop
SJU11:20 pmSan Juan Luis Munoz Marin Intl
Dec 25
SJU5:14 pmSan Juan Luis Munoz Marin Intl
6h 04m
MSP9:18 pmMinneapolis St Paul
$471
Find similar

JetBlue flights from Wisconsin to Caribbean Islands

Our best JetBlue deals on Wisconsin to Caribbean Islands flight tickets
JetBlue
Jan 13
ORD7:45 amChicago O'Hare Intl
8h 20m
1 stop
SJU6:05 pmSan Juan Luis Munoz Marin Intl
Jan 23
SJU11:06 amSan Juan Luis Munoz Marin Intl
10h 30m
1 stop
ORD7:36 pmChicago O'Hare Intl
$196
Find similar
JetBlue
Feb 27
ORD12:41 pmChicago O'Hare Intl
9h 03m
1 stop
SJU11:44 pmSan Juan Luis Munoz Marin Intl
Mar 7
SJU5:10 amSan Juan Luis Munoz Marin Intl
8h 48m
1 stop
ORD11:58 amChicago O'Hare Intl
$202
Find similar
JetBlue
Jan 31
ORD9:40 amChicago O'Hare Intl
7h 46m
1 stop
SJU7:26 pmSan Juan Luis Munoz Marin Intl
Feb 7
SJU1:30 pmSan Juan Luis Munoz Marin Intl
8h 15m
1 stop
ORD7:45 pmChicago O'Hare Intl
$205
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Wisconsin to Caribbean Islands that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated December 18, 2025.
Use the filters below to find and compare flights from Wisconsin to Caribbean Islands that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 2/21

9:18 am-7:43 pm

1 stop8h 25m

San Juan Luis Munoz Marin Intl

Mon 3/2

5:25 pm-11:15 pm

1 stop7h 50m

$195

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 1/13

7:45 am-6:05 pm

1 stop8h 20m

San Juan Luis Munoz Marin Intl

Fri 1/23

11:06 am-7:36 pm

1 stop10h 30m

$196

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 1/24

12:17 pm-6:49 pm

Nonstop4h 32m

San Juan Luis Munoz Marin Intl

Wed 2/4

1:22 pm-4:37 pm

Nonstop5h 15m

$197

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 2/7

9:25 am-4:21 pm

1 stop28h 56m

San Juan Luis Munoz Marin Intl

Tue 2/10

5:25 pm-3:52 pm

1 stop24h 27m

$198

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Thu 2/19

1:54 pm-2:25 am

1 stop10h 31m

San Juan Luis Munoz Marin Intl

Sun 2/22

2:54 am-9:11 am

1 stop8h 17m

$201

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 1/10

5:15 am-1:38 pm

1 stop7h 23m

George Town Owen Roberts Intl

Sat 1/17

2:34 pm-11:46 pm

1 stop10h 12m

$240

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Wed 2/25

5:45 am-12:30 pm

Nonstop4h 45m

Punta Cana

Sun 3/1

6:00 pm-9:10 pm

Nonstop5h 10m

$249

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sat 2/21

10:27 am-5:12 pm

Nonstop4h 45m

Punta Cana

Sat 2/28

5:47 am-8:57 am

Nonstop5h 10m

$251

ChicagoNassau

ORD - NAS

ORDNAS

Chicago O'Hare Intl

Sat 3/28

12:50 pm-12:15 pm

1 stop22h 25m

Nassau Intl

Fri 4/3

11:15 am-11:43 am

1 stop25h 28m

$356

ChicagoNassau

ORD - NAS

ORDNAS

Chicago O'Hare Intl

Sat 3/28

6:04 pm-12:15 pm

2 stops17h 11m

Nassau Intl

Fri 4/3

1:25 pm-8:00 am

2 stops19h 35m

$359

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Caribbean Islands from

How to get the cheapest flight ticket from Wisconsin to Caribbean Islands

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Caribbean Islands?

The month of September is, on average, the cheapest month to fly to Caribbean Islands from Wisconsin, with most prices found around $315. The month of October is another great option to travel to Caribbean Islands, with average flight prices from Wisconsin averaging around $350.

What is the cheapest day to depart on your flight to Caribbean Islands?

The cheapest day to depart from Wisconsin to Caribbean Islands is on a Tuesday. Travelers who choose to depart for Caribbean Islands on a Tuesday will often find tickets for as low as $389. If your travel schedule is flexible, try to avoid departing on a Friday because tickets tend to average around $477. These prices are subject to change though, so be sure to set up a Price Alert for flights to Caribbean Islands.

What is the cheapest time of day to depart on your flight to Caribbean Islands?

According to our data, the cheapest time of day to fly to Caribbean Islands is in the evening. momondo users have found flights departing from Wisconsin to Caribbean Islands in the evening for as low as $360. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. Try not to purchase tickets at noon because they tend to be around $458. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Wisconsin to Caribbean Islands flight route?

Fly from Milwaukee-Mitchell to Montego Bay Sangster Intl for the best Wisconsin - Caribbean Islands flight prices

How far in advance should I book a flight to Caribbean Islands?

You are more likely to see cheaper flights to Caribbean Islands from Wisconsin when booking weeks ahead of your departure date. In general, you can expect to find flights to Caribbean Islands for around $434 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Caribbean Islands from Wisconsin for as low as $343 on momondo.

What cabin class options are available on Wisconsin to Caribbean Islands flights?

There is only 1 cabin class available to choose from on Wisconsin to Caribbean Islands flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Wisconsin to Caribbean Islands flights?

No. A direct flight is the cheapest option for a flight between Wisconsin to Caribbean Islands.

Cheap Wisconsin to Caribbean Islands flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Wisconsin to Caribbean Islands

Fastest flight time

3h 25m

Direct flights

Every day

Airports in Caribbean Islands

99 airports
The fastest flight from Wisconsin to Caribbean Islands takes 3h 25m
Direct flights go from Wisconsin to Caribbean Islands every day.
There are 99 airports in Caribbean Islands. From Wisconsin there are direct flights to George Town Owen Roberts Intl (GCM), Nassau Intl (NAS), Montego Bay Sangster Intl (MBJ).
Search flight deals

  • When did momondo last update prices for flights from Wisconsin to Caribbean Islands?

    Prices for flights from Wisconsin to Caribbean Islands refresh daily.

  • How many operators does momondo search for flights from Wisconsin to Caribbean Islands?

  • How old do you have to be to fly from Wisconsin to Caribbean Islands?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Wisconsin to Caribbean Islands.

  • What documentation or ID do you need to fly to Caribbean Islands?

    The required travel and health documents for your Caribbean Islands trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Caribbean Islands. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular plane model from Wisconsin to Caribbean Islands?

Best airlines flying from Wisconsin to Caribbean Islands

Compare and see reviews for airlines that fly from Wisconsin to Caribbean Islands with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $129Free CancellationRating
5.8
3,081 reviews
Search Frontier flights
DeltaPriceFrom $191Free CancellationRating
7.9
8,007 reviews
Search Delta flights
United AirlinesPriceFrom $215Free CancellationRating
7.4
9,091 reviews
Search United Airlines flights
Spirit AirlinesPriceFrom $226Free CancellationRating
6.3
8,190 reviews
Search Spirit Airlines flights
American AirlinesPriceFrom $268Free CancellationRating
7.2
11,054 reviews
Search American Airlines flights
SouthwestPriceFrom $315Free CancellationRating
7.9
4,250 reviews
Search Southwest flights
Sun Country AirPriceFrom $497Free CancellationRating
6.9
333 reviews
Search Sun Country Air flights

Why use momondo?

Why should I use momondo to find a flight deal from Wisconsin to Caribbean Islands?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Wisconsin to Caribbean Islands. momondo saves you time and could save you money on your trip.

Can I find flights from Wisconsin to Caribbean Islands with flexible booking policies on momondo?

Yes. All flights to Caribbean Islands from Wisconsin on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Wisconsin to Caribbean Islands?

momondo provides multiple filters to help you find the best flight to Caribbean Islands from Wisconsin. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Wisconsin to Caribbean Islands right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Wisconsin to Caribbean Islands now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Caribbean Islands and let you know when they change.

An easier way to manage your Caribbean Islands trip

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